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Stereoselective Late-Stage Transformations of Indolo[2,3-a]quinolizines Skeleta to Nature-Inspired Scaffolds
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2021-09-03 , DOI: 10.1021/acs.joc.1c01523
Vunnam Srinivasulu 1 , Scott McN Sieburth 2 , Monther A Khanfar 3 , Imad A Abu-Yousef 4 , Amin Majdalawieh 4 , Mani Ramanathan 4 , Anusha Sebastian 1 , Taleb H Al-Tel 1, 5
Affiliation  

The indolo[2,3-a]quinolizines, canthines, and arborescidines natural products exhibit a wide range of bioactivities including anticancer, antiviral, antibacterial, and anti-inflammatory, among others. Therefore, the development of modular and efficient strategies to access the core scaffolds of these classes of natural products is a remarkable achievement. The Complexity-to-Diversity (CtD) strategy has become a powerful tool that transforms natural products into skeletal and stereochemical diversity. However, many of the reactions that could be utilized in this process are limited by the type of functional groups present in the starting material, which restrict transformations into a variety of products to achieve the desired diversity. In the course of employing a (CtD) strategy en route to the synthesis of nature-inspired compounds, unexpected stereoelectronic-driven rearrangement reactions have been discovered. These reactions provided a rapid access to indolo[2,3-a]quinolizines-, canthines-, and arborescidines-inspired alkaloids in a modular and diastereoselective manner. The disclosed strategies will be widely applicable to other late-stage natural product transformation programs and drug discovery initiatives.

中文翻译:

Indolo[2,3-a]喹啉骨架到自然支架的立体选择性后期转化

indolo[2,3- a]喹嗪类、角类化合物和阿波西啶类天然产物具有广泛的生物活性,包括抗癌、抗病毒、抗菌和抗炎等。因此,开发模块化和高效的策略来获取这些天然产物的核心支架是一项了不起的成就。复杂性到多样性 (CtD) 策略已成为将天然产物转化为骨架和立体化学多样性的有力工具。然而,该过程中可以使用的许多反应都受到起始材料中存在的官能团类型的限制,这限制了转化为各种产品以实现所需的多样性。在采用 (CtD) 策略合成受自然启发的化合物的过程中,发现了意想不到的立体电子驱动的重排反应。这些反应提供了快速获得吲哚[2,3-模块化和非对映选择性方式获得喹啉嗪、角莨菪碱和木犀草素启发的生物碱。所披露的策略将广泛适用于其他后期天然产物转化计划和药物发现计划。
更新日期:2021-09-17
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